U.S. patent number 8,236,195 [Application Number 12/351,651] was granted by the patent office on 2012-08-07 for fluorine-containing curable composition.
This patent grant is currently assigned to Shin-Etsu Chemical Co., Ltd.. Invention is credited to Noriyuki Koike, Yasunori Sakano.
United States Patent |
8,236,195 |
Sakano , et al. |
August 7, 2012 |
Fluorine-containing curable composition
Abstract
A fluorine-containing curable composition containing (A) A
fluorine-containing amino compound having primary or secondary
amino groups at both ends, said compound being represented by the
formula (1): Y-Q-Rf--(X--Rf).sub.n-Q-Y (1) wherein Rf is a divalent
perfluorooxyalkylene group, each Q is independently a divalent
organic group having 1 to 20 carbon atoms and, optionally,
containing an oxygen atom and/or a nitrogen atom, X is a divalent
organic group having 1 to 20 carbon atoms and, optionally,
containing an oxygen atom and/or a nitrogen atom, Y is an organic
group having a primary or secondary amino group and 1 to 20 carbon
atoms and, optionally, containing an oxygen atom, and n is an
integer of from 1 to 20, (B) An epoxy compound having at least two
epoxy groups in a molecule, in an amount such that the amount of
the epoxy groups is 0.1 to 10 moles per mole of the amino groups of
component (A), and (C) At least one alcohol containing fluorine
atoms and represented by the following formula (2) in an amount
such that the amount of the alcoholic hydroxyl group is 0.001 to
0.5 mole per mole of the amino groups of component (A):
Rf'(CH.sub.2OH).sub.m (2), wherein m is an integer of 1 or 2, Rf'
is a monovalent or divalent group containing 2 to 300 fluorine
atoms, and at least one fluorine atom or at least one
trifluoromethyl group is bonded to a carbon atom to which site the
methylol group is bonded.
Inventors: |
Sakano; Yasunori (Annaka,
JP), Koike; Noriyuki (Takasaki, JP) |
Assignee: |
Shin-Etsu Chemical Co., Ltd.
(Tokyo, JP)
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Family
ID: |
40849847 |
Appl.
No.: |
12/351,651 |
Filed: |
January 9, 2009 |
Prior Publication Data
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Document
Identifier |
Publication Date |
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US 20090179174 A1 |
Jul 16, 2009 |
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Foreign Application Priority Data
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Jan 16, 2008 [JP] |
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2008-007286 |
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Current U.S.
Class: |
252/182.15;
528/121; 528/401; 528/119; 528/123 |
Current CPC
Class: |
C08G
65/33317 (20130101); C08L 71/02 (20130101); C08G
65/007 (20130101); C08G 59/504 (20130101); C08L
71/02 (20130101); C08L 2666/22 (20130101); C08G
2650/48 (20130101); C08L 63/00 (20130101) |
Current International
Class: |
C09K
3/00 (20060101); C08G 59/40 (20060101); C08G
59/50 (20060101); C08G 59/62 (20060101); C08G
59/00 (20060101) |
Field of
Search: |
;528/119,121,123,401
;252/182.15 |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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8-199070 |
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Aug 1996 |
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JP |
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9-077777 |
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Mar 1997 |
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JP |
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11-092547 |
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Apr 1999 |
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JP |
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2007-119688 |
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May 2007 |
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JP |
|
Primary Examiner: Godenschwager; Peter F
Attorney, Agent or Firm: Birch, Stewart, Kolasch & Birch
LLP
Claims
The invention claimed is:
1. A method for curing a fluorine-containing curable composition
containing (A) a fluorine-containing amino compound having primary
or secondary amino groups at both ends, said compound being
represented by the formula (1): Y-Q-Rf--(X--Rf).sub.n-Q-Y (1)
wherein Rf is a divalent perfluorooxyalkylene group, each Q is
independently a divalent organic group having 1 to 20 carbon atoms
and, optionally, containing an oxygen atom and/or a nitrogen atom,
X is a divalent organic group having 1 to 20 carbon atoms and,
optionally, containing an oxygen atom and/or a nitrogen atom, Y is
an organic group having a primary or secondary amino group and 1 to
20 carbon atoms and, optionally, containing an oxygen atom, and n
is an integer of from 1 to 20, and (B) an epoxy compound having at
least two epoxy groups in a molecule, in an amount such that the
amount of the epoxy groups is 0.8 to 2 moles per mole of the amino
groups of component (A), and wherein the method comprises the steps
of adding (C) at least one alcohol containing fluorine atoms to the
aforesaid fluorine-containing curable composition in an amount such
that the amount of the alcoholic hydroxyl group is 0.01 to 0.2 mole
per mole of the amino groups of component (A), wherein the alcohol
is represented by the following formula (2): Rf'(CH.sub.2OH).sub.m
(2) wherein m is an integer of 1 or 2, Rf' is a monovalent or
divalent group containing 2 to 300 fluorine atoms, and at least one
fluorine atom or at least one trifluoromethyl group is bonded to a
carbon atom to which the methylol group is bonded, and allowing the
composition to cure, wherein (C) the alcohol containing fluorine
atoms, works as a catalyst.
2. The method for curing the fluorine-containing curable
composition according to claim 1, wherein the site of Rf' to which
the methylol group is bonded is represented by one of the following
formulas (i) to (iii): --CF.sub.2-- (i) --CF(CF.sub.3)-- (ii)
--C(CF.sub.3).sub.2-- (iii).
3. The method for curing the fluorine-containing curable
composition according to claim 1 or 2, wherein said Rf' is a
perfluoroalkylene or perfluorooxyalkylene group having 1 to 6
carbon atoms.
4. The method for curing the fluorine-containing curable
composition according to claim 1 or 2, wherein said
fluorine-containing alcohol has a number average molecular weight
of 700 to 10,000.
5. The method for curing the fluorine-containing curable
composition according to claim 4, wherein said fluorine-containing
alcohol is represented by the following formula (3):
OHCH.sub.2CF.sub.2O(CF.sub.2CF.sub.2O).sub.p(CF.sub.2O).sub.qCF.sub.2CH.s-
ub.2OH (3) wherein p and q are an integers such that the number
average molecular weight of the fluorine-containing alcohol is from
700 to 10,000, and the repeating units (CF.sub.2CF.sub.2O) and
(CF.sub.2O) may randomly be distributed.
6. The method for curing the fluorine-containing curable
composition according to claim 1, wherein said Rf in formula (1) is
represented by the following formula: ##STR00020## wherein each of
a and b is independently an integer from 1 to 200, an average of
a+b is 2 to 200, and each of c and d is independently an integer of
from 1 to 4.
7. The method for curing the fluorine-containing curable
composition according to claim 1, wherein said Q in formula (1) is
a group represented by any of the following formulas: ##STR00021##
wherein R.sup.1 is a hydrogen atom or a monovalent hydrocarbon
group having 1 to 20 carbon atoms, wherein a part of the hydrogen
atoms may be substituted with a fluorine atom, and e is an integer
of from 0 to 6, X is a group represented by any of the following
formulas: ##STR00022## wherein R.sup.1 is as defined above, and m
is an integer of from 1 to 6, and Y is a group represented by the
following formula: ##STR00023##
8. The method for curing the fluorine-containing curable
composition according to claim 1, wherein said m is 1.
Description
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a fluorine-containing curable
composition, more specifically a three-liquid or two-liquid type
curable composition which cures more rapidly at room temperature,
compared to conventional ones, on account of incorporation of a
fluorine-containing alcohol.
2. Description of the Prior Art
Epoxy resins cure easily at a temperature of from room temperature
to about 100.degree. C., without causing by-products of a low
molecular weight in curing. Accordingly, they are used widely in
molded articles, sealants, and adhesives. However, because the
epoxy resins show poor solvent resistance and chemical resistance,
they are unsuitable to applications where they might be in contact
with chemicals.
Meanwhile, fluorine-containing compounds, especially
perfluoro-polyethers, have excellent resistance to solvents and to
chemicals, and are used in curable compositions. For example,
Japanese Patent Application Laid-Open No. 08-199070/1996 discloses
a composition to be cured via a hydrosilylation reaction between a
perfluoro-polyether compound having a terminal vinyl group and a
compound having an Si--H group. Japanese Patent Application
Laid-Open No. 09-077777/19967 discloses a perfluoro-polyether
composition curable via a condensation reaction. However, the
former has a problem that properties of a resultant cured material,
such as chemical resistance, vary largely, depending upon species
and amounts of a curing catalyst and a reaction controlling agent,
because the hydrosilylation reaction is carried out at or below a
temperature of 100 degrees Centigrade. The latter composition may
cause an environment concern because low molecular weight
by-products occur in the condensation reaction, such as alcohols
and ketones.
Japanese Patent Application Laid-Open No. 11-092547/1999 discloses
a curable composition containing a perfluoro-polyether compound
having secondary amino groups at both ends of the fluoro-polyether
and a fluorine-containing compound having at least three epoxy
groups in a molecule. That curable composition is curable even at
room temperature to give a cured material which shows a small
change in volume in various solvents and high resistance to
solvents and chemicals. However, its curing rate at room
temperature is not satisfactory, so that improvement is
desirable.
SUMMARY OF THE INVENTION
A purpose of the present invention is to provide a
fluorine-containing curable composition which can be cured in a
shorter period of time, compared to conventional ones, even at room
temperature to attain a curd material excellent in solvent
resistance and chemical resistance.
The present invention is a fluorine-containing curable composition
containing
(A) A fluorine-containing amino compound having primary or
secondary amino groups at both ends, said compound being
represented by the formula (1): Y-Q-Rf--(X--Rf).sub.n-Q-Y (1)
wherein Rf is a divalent perfluorooxyalkylene group,
each Q is independently a divalent organic group having 1 to 20
carbon atoms and, optionally, containing an oxygen atom and/or a
nitrogen atom,
X is a divalent organic group having 1 to 20 carbon atoms and,
optionally, containing an oxygen atom and/or a nitrogen atom,
Y is an organic group having a primary or secondary amino group and
1 to 20 carbon atoms and, optionally, containing an oxygen atom,
and
n is an integer of from 1 to 20,
(B) An epoxy compound having at least two epoxy groups in a
molecule, in an amount such that the amount of the epoxy groups is
0.1 to 10 moles per mole of the amino groups of component (A),
and
(C) At least one alcohol containing fluorine atoms and represented
by the following formula (2) in an amount such that the amount of
the alcoholic hydroxyl group is 0.001 to 0.5 mole per mole of the
amino groups of component (A): Rf'(CH.sub.2OH).sub.m (2)
wherein m is an integer of 1 or 2, Rf' is a monovalent or divalent
group containing 2 to 300 fluorine atoms, and at least one fluorine
atom or at least one trifluoromethyl group is bonded to a carbon
atom to which the methylol group is bonded.
The fluorine-containing alcohol in the present composition promotes
curing of the composition, so that a curing rate at room
temperature is higher than that of conventional compositions.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
Because the present composition cures even at room temperature,
components (A), (B) and (C) are usually provided separately in a
form of three-liquid type or in two-liquid type with (B) and a
mixture of (A) and (C). These are mixed together immediately before
use to form one liquid. Thus, the two-liquid type of the
composition comprises
(I) a first liquid which comprises the fluorine-containing amino
compound having primary or secondary amino groups at both ends,
represented by the formula (1) and at least one alcohol containing
fluorine atoms and represented by the formula (2) in an amount such
that the amount of the alcoholic hydroxyl group is 0.001 to 0.5
mole per mole of the amino groups of component (A), and (II) a
second liquid which comprises the epoxy compound having at least
two epoxy groups in a molecule. These are provided simultaneously
or separately and used in an amount such that the amount of the
epoxy groups of the second liquid is 0.1 to 10 moles per mole of
the amino groups of the first liquid.
If the components are delivered and stored at a low temperature,
these may be in a form of one-liquid type. In a two-liquid type, it
is possible to have component (C) mixed in the component (B), epoxy
compound. However, component (C) is preferably mixed with (A) the
fluorine-containing amino compound, on account of compatibility.
Any mixing means may be used, such as mixers and kneaders.
The fluorine-containing amino compound having primary or secondary
amino groups at both ends is represented by the following formula
(1): Y-Q-Rf--(X--Rf).sub.n-Q-Y (1)
wherein Rf is a divalent perfluorooxyalkylene group, preferably a
perfluorooxyalkylene group comprising repeating units composed of a
fluoroalkylene group having at most three carbon atoms and an
oxygen atom. Examples of such repeating units may be ones
represented by the following formula. Plural kinds of the repeating
units represented by the formula may be present together.
--(C.sub.nF.sub.2nO)--
wherein is an integer of from 1 to 3, and the repeating units may
be branched.
A particularly preferred Rf has the following structure:
##STR00001##
wherein a and b are independently an integer of from 1 to 200,
preferably from 1 to 150, provided that an average of a+b is 2 to
200, preferably 10 to 150, and c and d are independently an integer
of from 1 to 4.
X in formula (1) is a divalent group having 1 to 20 carbon atoms
and, optionally, containing an oxygen atom and/or a nitrogen atom.
When n is 2 or larger, X may be different from each other. X may be
as follows:
##STR00002##
wherein e is an integer of from 0 to 6, and each R.sup.1 is
independently a hydrogen atom or a monovalent hydrocarbon group
with 1 to 14 carbon atoms.
Among these, particularly preferred are the following groups:
##STR00003##
Examples of R.sup.1 include a hydrogen atom; unsubstituted
monovalent hydrocarbon groups, such as alkyl groups such as methyl,
ethyl, propyl, butyl, hexyl, cyclohexyl, octyl and decyl groups;
alkenyl groups such as vinyl, ally, propenyl, butenyl and hexenyl
groups; aryl groups such as phenyl, tolyl, xylyl and naphtyl
groups; and aralkyl groups such as benzyl and phenylethyl groups,
or these groups in which a part or the whole of the hydrogen atoms
are substituted with a fluorine atom(s), preferred are a hydrogen
atom, and methyl, ethyl and aryl groups.
Y in formula (1) is an organic group which has a primary or
secondary amino group and 1 to 20 carbon atoms and, optionally,
contains an oxygen atom. Examples of Y include the following:
##STR00004##
wherein e and R.sup.1 are as defined above.
R.sup.2 in the aforesaid formula is a divalent hydrocarbon group
having 1 to 20 carbon atoms, and may be partly substituted with a
fluorine atom(s). Examples of it include a methylene, ethylene,
propylene and butylenes groups and the following groups:
##STR00005##
Among these, particularly preferred are
##STR00006##
Q in formula (1) is independently a divalent organic group having 1
to 20 carbon atoms, which may optionally contain an oxygen atom
and/or a nitrogen atom, such as
##STR00007##
wherein e and R.sup.1 are as defined above.
Among these, particularly preferred are:
##STR00008##
Particularly preferred examples of the fluorine-containing amino
compound represented by formula (1) are the following ones or
mixtures thereof.
##STR00009##
wherein an average of a is 0 to 2,
##STR00010##
wherein
Rf:
##STR00011##
wherein an average of a is 0 to 2, and an average of n+m is 10 to
150,
##STR00012##
wherein
Rf:
##STR00013##
wherein an average of n+m is 10 to 150.
Examples of the compound having at least two epoxy groups in a
molecule (B) include bisphenol A epoxy resins, bisphenol F epoxy
resins, bisphenol AF epoxy resins, phenol novolak epoxy resins,
hydrogenated bisphenol A epoxy resins, glycidyl amines such as
triglycidyl-p-aminophenol, and diglycidyl aniline; aliphatic epoxy
resins such as polypropyleneglycol diglycidylether,
trimethylolpropane triglycidylether, pentaerythritol
polyglycidylether, and glycerine triglycidylether; trigycidyl
isocyanurate; and epoxy compounds having the following
structures:
##STR00014## ##STR00015##
Among these, particularly preferred are bisphenol A epoxy resins,
bisphenol F epoxy resins, bisphenol AF epoxy resins, hydrogenated
bisphenol A epoxy resins, triglycidyl-p-aminophenol, diglycidyl
aniline, trimethylolpropane triglycidylether, pentaerythritol
polyglycidylether, and glycerine triglycidylether.
The composition of the invention shows a higher curing rate,
compared to prior art fluorine-containing compounds, as the
composition comprises the fluorine-containing alcohol (C). It is
believed that this is because the fluorine atom or trifluorometyl
group bonded to a carbon atom adjacent to a methylol group acts as
an electron-withdrawing group to have a proton of the methylol
group work as acidic catalyst, though the invention shall not be
limited by this theory. In this point, the composition of the
present invention differs from the composition of Japanese Patent
Application Laid-Open No. 2007-119688, which comprises an epoxy
resin modified with a fluorine-containing alcohol.
The fluorine-containing alcohol used in the present invention is
represented by the following formula (2): Rf'(CH.sub.2OH).sub.m (2)
wherein m is 1 or 2, Rf' is a monovalent or divalent group
containing 2 to 300 fluorine atoms, and at least one fluorine atom
or at least one trifluoromethyl group is bonded to a carbon atom to
which the methylol group is bonded. A site of Rf' to which site the
methylol group is bonded is preferably represented by any of the
following formulas (i) to (iii): --CF.sub.2-- (i) --CF(CF.sub.3)--
(ii) and --C(CF.sub.3).sub.2-- (iii).
In the formulas (i) to (iii), the remaining moiety of Rf' from
which the terminal carbon atom is excepted is attached to the side
opposite the side on which the methylol group is bonded. This
remaining moiety may be a hydrogen or fluorine atom. In formula
(2), m=2. When Rf' is a divalent group, another methylol group may
be bonded. That is, the fluorine-containing alcohol may be ones
represented by the following formulas:
##STR00016##
Preferred fluorine-containing alcohol may be (1) such that Rf' is a
monovalent or divalent perfluorchydrocarbon having 1 to 6 carbon
atoms, or (2) one having polyether structure and having a number
average molecular weight of 700 to 10,000, more preferably 800 to
6,000. The aforesaid (1) is suitable to applications which require
that a less amount of the fluorine-containing alcohol is added not
to remain in a cured material. The aforesaid (2) is suitable to
applications which require less curing shrinkage of a cured
material.
Examples of the monovalent Rf' in the alcohol (1) include
fluorinated alkyl groups and fluorinated oxyalkyl groups as
follows: CF.sub.3C.sub.nF.sub.2n--
wherein n is an integer of from 0 to 5, and Rf' may be branched,
CF.sub.3(CHF).sub.m(CF.sub.2).sub.n--
wherein m is an integer of from 1 to 5, n is an integer of from 0
to 5, at least one (CF.sub.2) exists at the terminal, and the
remaining (CF.sub.2) and (CHF) may be distributed at random,
HCF.sub.2(CF.sub.2).sub.n--
wherein n is an integer of from 0 to 5.
Examples of the divalent Rf' in the alcohol (1) include fluorinated
alkylene groups and fluorinated oxyalkylene groups as follows:
--C.sub.nF.sub.2n--
wherein n is an integer of from 1 to 6, and Rf' may be branched,
--CF.sub.2(C.sub.mF.sub.2mO)CF.sub.2--
wherein m is an integer of from 1 to 4, and Rf' may be
branched.
Examples of the monovalent Rf' in the alcohol (2) having polyether
structure include:
CF.sub.3OC.sub.nF.sub.2n(CF.sub.2CF.sub.2O).sub.kCF.sub.2--
wherein n is 0 or 1, k is an integer of from 1 to 100, preferably
from 1 to 50.
Examples of the divalent Rf' include:
--CF.sub.2(C.sub.mF.sub.2mO).sub.kCF.sub.2--
wherein m is an integer of from 1 to 4, and k is as defined above,
and Rf' may be branched,
--CF.sub.2O(CF.sub.2CF.sub.2O).sub.p(CF.sub.2O).sub.qCF.sub.2--
wherein p and q are integers to give a number average molecular
weight of the fluorine-containing alcohol of 700 to 10,000,
preferably 800 to 6,000, and the repeating units
(CF.sub.2CF.sub.2O) and (CF.sub.2O) may be distributed at
random.
In the present composition, the fluorine-containing amino compound
and the epoxy compound are contained in such amounts that the
amount of the epoxy groups of the epoxy compound is 0.1 to 10
moles, preferably 0.5 top 3 moles, more preferably 0.8 to 2 moles,
per mole of the amino groups of the fluorine-containing amino
compound. If the amount of the epoxy compound is outside the
aforesaid range, poor curing may take place.
The fluorine-containing alcohol I used in such an amount that the
amount of the alcoholic hydroxyl group of the fluorine-containing
alcohol is 0.001 to 0.5 mole, preferably 0.005 to 0.3 mole, more
preferably 0.01 to 0.2 mole, per mole of the amino groups of the
fluorine-containing amino compound. If the amount of the
fluorine-containing alcohol is less than the aforesaid lower limit,
the improvement on the curing rate is insufficient, so that
problems such as bleeding may take place.
The fluorine-containing curable composition of the invention may
comprise, besides the aforesaid components, various conventional
additives, if desired, as far as the purpose of the invention is
not disturbed to attain. The additives may be added after the
essential components are blended, or may be added to any liquid of
a three-liquid or two-liquid system in advance. Those additives
include cure-promoting agents such as tertiary amine compounds and
imidazoles, carbon black such as acetylene black, reinforcing
agents such as fumed silica, precipitated silica, titanium dioxide,
aluminum oxide, quartz powder, carbon powder, talc and bentonite,
fiber fillers such as asbestos, glass fiber and organic fiber,
coloring agents such as pigments and dyes, heat
resistance-improving agents such as red iron oxide and cerium
oxide, cold-resistance improving agents, antirust agents,
adhesion-improving agents such as .beta.-(3,4-epoxycyclohexyl)ethyl
trimethoxysilane, .gamma.-glycidoxy propyltriethoxysilane, and
.gamma.-amino propyltriethoxysilane, and fluorinated or
non-fluorinated nomofunctional epoxy compounds.
The present composition may be mixed by any known means, for
instance, such as a mixer or a kneader. The mixed composition may
be applied on various substrates such as metals, plastics,
ceramics, and glass. In the application, the composition may be
made in a desired concentration by a fluoric solvent such as
1,3-bistrifluoromethy benzene and perfluorooctane. Alternatively,
the first liquid and the second liquid are each in a form
separately dissolved in a solvent.
The composition of the invention is capable of curing in a shorter
period of time, compared to prior art curable compositions. The
composition is useful in additives or sealants for electronic
components which are not allowed to be heated. The composition can
be cured in several minutes to several hours by heating at 50 to
200 degrees Centigrade. The composition is further useful in
sealing materials, coating materials, tent coating material and
potting materials.
EXAMPLES
Room Temperature Curing Test
Were mixed the following epoxy component, amine component, and
alcohol component on a glass petri dish, and left at room
temperature. Then, its surface was scratched manually with a
spatula every three hours after the completion of the mixing. The
time when the flowability of the surface disappeared was recorded
as a curing time. The results are as shown in Table 1. The
components in the table are as follows.
(A) Fluorine-Containing Amino Compound
##STR00017##
wherein the average of r is 0.1, and
Rf is represented by the following formula:
##STR00018##
wherein the average of n+m is 35.
(B) Epoxy Compound
##STR00019## (C-1) Fluorine-Containing Alcohol
HO--CH.sub.2--CF.sub.2O--(CF.sub.2CF.sub.2O).sub.s(CF.sub.2O).sub.t--CF.s-
ub.2--CH.sub.2--OH
wherein s and t are such numbers as to give an average molecular
weight of 1,000.
(C-2) Fluorine-Containing Alcohol
HO--CH.sub.2--CF.sub.2O--(CF.sub.2CF.sub.2O).sub.u(CF.sub.2O).sub.v--CF.s-
ub.2--CH.sub.2--OH
wherein u and v are such numbers as to give an average molecular
weight of 2,000.
(C-3) Fluorine-Containing Alcohol CF.sub.3CH.sub.2OH
TABLE-US-00001 TABLE 1 Composition, part by weight Ex. 1 Ex. 2 Ex.
3 Comp. 1 A 100 100 100 100 B 4 4 4 4 C-1 1.8 -- -- -- C-2 -- 3.6
-- -- C-3 -- -- 0.18 Amino group/ 1.00/ 1.00/ 1.00/ 1.00/ Epoxy
group/ 1.38/ 1.38/ 1.38/ 1.38/ OH group, mole ratio 0.114 0.114
0.114 0 Curing time, hr. 24 27 21 39
As seen from Table 1, the curing rate of the present composition is
higher, compared to that of Comparative Example, on account of the
incorporation of the fluorine-containing alcohol.
INDUSTRIAL APPLICABILITY
The curable composition of the present invention cures rapidly even
at room temperature, and is useful in adhesives and sealing agents
for electronic components which are not allowed to be heated.
* * * * *